CN101412710B - Omeprazole sodium compound and preparation thereof - Google Patents
Omeprazole sodium compound and preparation thereof Download PDFInfo
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- CN101412710B CN101412710B CN2008101834096A CN200810183409A CN101412710B CN 101412710 B CN101412710 B CN 101412710B CN 2008101834096 A CN2008101834096 A CN 2008101834096A CN 200810183409 A CN200810183409 A CN 200810183409A CN 101412710 B CN101412710 B CN 101412710B
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- omeprazole sodium
- adsorbent resin
- macroporous adsorbent
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- 229940063517 omeprazole sodium Drugs 0.000 title claims abstract description 40
- KNVABRFVZVESIL-UHFFFAOYSA-N sodium;6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound [Na+].N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C KNVABRFVZVESIL-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 43
- 239000011347 resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 22
- 239000000047 product Substances 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000011973 solid acid Substances 0.000 claims abstract description 6
- 238000001291 vacuum drying Methods 0.000 claims abstract description 6
- 239000012043 crude product Substances 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 17
- 230000001105 regulatory effect Effects 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003463 adsorbent Substances 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 229960001701 chloroform Drugs 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 239000008213 purified water Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 claims description 2
- -1 Citric Acid hydrogen salt Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000011001 backwashing Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000012046 mixed solvent Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- KYKNRZGSIGMXFH-UHFFFAOYSA-M potassium;2,3-dihydroxybutanedioate;hydron Chemical compound [K+].OC(=O)C(O)C(O)C([O-])=O KYKNRZGSIGMXFH-UHFFFAOYSA-M 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Abstract
The invention relates to an omeprazole sodium compound and a method for preparing the same. The method comprises the following steps: dissolving an omeprazole sodium crude product in water, adding solution of a solid acid salt into the mixture, collecting the precipitated solid, dissolving the solid by using an organic solvent, eluting and purifying the mixture by an eluant through macroporous resin, collecting the eluate, adding an alkaline solution into the eluate to regulate the pH value to be alkaline, collecting the precipitated solid, and performing vacuum drying on the solid after washing to obtain the refined product of the omeprazole sodium. The purity of the omeprazole sodium prepared by the method is more than 99.8 percent, thus the purity and the preparation stability of the omeprazole sodium product are greatly improved.
Description
Technical field
The present invention relates to a kind of omeprazole sodium compound method for making, belong to medical technical field.
Background technology
Omeprazole Sodium, its chemical name is: 5-methoxyl group-2-{[(4-methoxyl group-3,5-dimethyl-2-pyridyl)-methyl]-sulfinyl }-1H-benzoglyoxaline sodium-hydrate, structural formula is:
It is the hydrochloric acid in gastric juice proton pump inhibitor that is widely used in treating digestive tract ulcer in recent years.
At present existing a lot of patents the reported for work preparation method and the application of omeprazole and salt thereof, for example US4255431A, US4689333A, EP0533264A etc., method comprises single solvent crystallization process, mixed solvent crystallization method, acid-base method etc.Chinese patent application 95111640.1 also discloses the method that a kind of ion-exchange-resin process obtains Omeprazole Sodium; Chinese patent application 96116288.0 discloses a kind of method of utilizing the refining Omeprazole Sodium of activated carbon decolorizing method.The disclosed Omeprazole Sodium of prior art is made with extra care purification process, and the Omeprazole Sodium purity that obtains is still relatively poor, causes the preparation stability of Omeprazole Sodium to decline to a great extent, and has influenced its clinical application.
Summary of the invention
Therefore, the process for purification that the purpose of this invention is to provide a kind of Omeprazole Sodium.The inventive method has improved the purity of Omeprazole Sodium, has improved the product formulation quality.
For achieving the above object, technical solution of the present invention is as follows:
The invention provides a kind of process for purification of Omeprazole Sodium, it is characterized in that comprising the steps: that (1) is water-soluble with the Omeprazole Sodium crude product, regulating the pH value is that slightly acidic is extremely neutral, collects the solid of separating out; (2) with step (1) gained solid with organic solvent dissolution after, with eluent wash-out purifying, collect elutriant through macroporous adsorbent resin; (3) with step (2) gained elutriant, regulating the pH value is alkalescence, collects the solid of separating out, and obtains the Omeprazole Sodium highly finished product.
Wherein, above-mentioned described method, regulating the pH value in the preferred steps (1) is 5.5～7.5, more preferably 6.5～7.0.
Wherein, above-mentioned described method is regulated the pH value in the step (1), preferably adopts solid acid salt, for example a kind of or two or more in hydrosulfate, bitartrate, hydrophosphate, the Citric Acid hydrogen salt.
Method of the present invention, wherein said macroporous adsorbent resin preferably adopts styrene tyle macroporous adsorption resin; More preferably described macroporous adsorbent resin is D101 type macroporous adsorbent resin or AB-8 type macroporous adsorbent resin.
Aforesaid method, wherein eluent described in the macroporous adsorbent resin wash-out purifying in the step (2) is selected one or more mixed solvents in trichloromethane, methylene dichloride, ethyl acetate, acetone, the sherwood oil for use; Wherein more preferably described eluent is a trichloromethane.
Above-mentioned described method, the described organic solvent of dissolving Omeprazole Sodium in the step (2), be not particularly limited, for example can be one or more the mixed solvent in methylene dichloride, ethanol, methyl alcohol, trichloromethane, ethyl acetate, acetone, the sherwood oil; The preferred described organic solvent of the present invention is selected from methylene dichloride, ethanol, methyl alcohol.
Method of the present invention wherein in the step (3), selects for use the alkaline pH conditioning agent to regulate the pH value of elutriant, preferred alkaline carbonate or the supercarbonate of adopting more preferably adopts sodium bicarbonate or saleratus, regulates the pH value to alkalescence, be preferably 9.0～11.0, more preferably 9.5～10.5.
As the present invention's one preferred embodiment, the invention provides a kind of process for purification of Omeprazole Sodium, it is characterized in that comprising the steps: that (1) is water-soluble with Omeprazole Sodium, the solution adjusting pH value that adds solid acid salt is 6.5～7.0, insolubles is separated out in stirring, filter, obtain solid after the purified water washing; (2),,, collect elutriant with trichloromethane wash-out purifying through D101 macroporous adsorbent resin or AB-8 macroporous adsorbent resin with step (1) gained solid organic solvent dissolution; (3) step (2) gained elutriant being regulated pH value with sodium bicarbonate or saleratus is 9.5～10.5, separates out solid, centrifugal back washing with alcohol, and 30～40 ℃ of vacuum-drying 6～10 hours must the Omeprazole Sodium highly finished product.
Compare with existing Omeprazole Sodium preparation method, the inventive method can high yield, high purity obtains the Omeprazole Sodium highly finished product.Omeprazole Sodium process for purification of the present invention can obtain purity and reach Omeprazole Sodium elaboration more than 99.8%, and yield surpasses 90%.With respect to existing Omeprazole Sodium process for purification, obtain remarkable invention effect.The inventive method can obtain a kind of high-purity Omeprazole Sodium, thereby can improve omeprazol sodium preparation stability and clinical application effect.The inventive method is simple, easy handling, is suitable for big industrial production.
Embodiment
Below further explain and describe content of the present invention by embodiment, but embodiment is not to be construed as limiting the scope of the invention.
Used D101 macroporous resin of following examples and AB-8 macroporous resin are available from Liaoyuan, Bengbu novel material company limited.
Embodiment 1
The 100g Omeprazole Sodium is dissolved in 1000ml water, add the 2M sodium bisulfate, regulating the pH value is 6.8, insolubles is separated out in stirring, filters, with the washing of 200ml purified water, in the gained solid, add the 220ml methylene dichloride then and make its dissolving, add the pillar that is filled with the D101 macroporous resin and pass through, use trichloromethane wash-out pillar again, collect elutriant, regulating the pH value with the 5M sodium hydrogen carbonate solution is 10.5, separate out solid, whizzer is centrifugal, uses the 200ml washing with alcohol, 40 ℃ of vacuum-drying 6 hours, get Omeprazole Sodium highly finished product 91.7g, yield 91.7%, purity is 99.9%.
Embodiment 2
The 100g Omeprazole Sodium is dissolved in 800ml water, add 5M hydrogen tartrate potassium solution, regulating the pH value is 6.6, insolubles is separated out in stirring, filters, with the washing of 230ml purified water, in the gained solid, add 350ml ethanol then and make its dissolving, add the pillar that is filled with the AB-8 macroporous resin and pass through, use trichloromethane wash-out pillar again, collect elutriant, regulating the pH value with the 2M potassium bicarbonate solution is 9.7, separate out solid, whizzer is centrifugal, uses the 200ml washing with alcohol, 35 ℃ of vacuum-drying 10 hours, get Omeprazole Sodium highly finished product 92.2g, yield 92.2%, purity is 99.9%.
Embodiment 3
The 100g Omeprazole Sodium is dissolved in 1200ml water, add the 1M disodium phosphate soln, regulating the pH value is 6.5, insolubles is separated out in stirring, filters, with the washing of 200ml purified water, in the gained solid, add 270ml methyl alcohol then and make its dissolving, add the pillar that is filled with the D101 macroporous resin and pass through, use trichloromethane wash-out pillar again, collect elutriant, regulating the pH value with the 5M sodium hydrogen carbonate solution is 10.0, separate out solid, whizzer is centrifugal, uses the 300ml washing with alcohol, 40 ℃ of vacuum-drying 8 hours, get Omeprazole Sodium highly finished product 90.1g, yield 90.1%, purity is 99.8%.
According to the above embodiments the present invention has been made detailed description.It should be noted that above embodiment is just to illustrating the present invention.Under the prerequisite that does not depart from spirit of the present invention and essence, those skilled in the art can design multiple alternative of the present invention and improvement project, and it all should be understood to be within protection scope of the present invention.
Claims (16)
1. the process for purification of the omeprazole sodium compound of structure shown in the formula (I),
It is characterized in that comprising the steps: that (1) is water-soluble with the Omeprazole Sodium crude product, regulating the pH value is that slightly acidic is extremely neutral, collects the solid of separating out; (2) with step (1) gained solid with organic solvent dissolution after, with eluent wash-out purifying, collect elutriant through macroporous adsorbent resin; (3) with step (2) gained elutriant, regulating the pH value is alkalescence, collects the solid of separating out, and obtains the Omeprazole Sodium highly finished product.
2. method according to claim 1 is characterized in that regulating the pH value in the step (1) is 5.5～7.5.
3. method according to claim 2 is characterized in that described pH value is 6.5～7.0.
4. according to each described method of claim 1-3, it is characterized in that adopting in the step (1) solid acid salt to regulate the pH value.
5. method according to claim 4 is characterized in that described solid acid salt is selected from a kind of or two or more in hydrosulfate, bitartrate, hydrophosphate, the Citric Acid hydrogen salt.
6. according to each described method of claim 1-3, it is characterized in that macroporous adsorbent resin is a styrene tyle macroporous adsorption resin described in the step (2).
7. method according to claim 6 is characterized in that described macroporous adsorbent resin is D101 type macroporous adsorbent resin or AB-8 type macroporous adsorbent resin.
8. according to each described method of claim 1-3, it is characterized in that eluent described in the step (2) is selected from one or more in trichloromethane, methylene dichloride, ethyl acetate, acetone, the sherwood oil.
9. method according to claim 8 is characterized in that described eluent is a trichloromethane.
10. according to each described method of claim 1-3, it is characterized in that organic solvent described in the step (2) is selected from one or more in methylene dichloride, ethanol, methyl alcohol, trichloromethane, ethyl acetate, acetone, the sherwood oil.
11. method according to claim 10 is characterized in that described organic agent is selected from methylene dichloride, ethanol, methyl alcohol.
12., it is characterized in that regulating the pH value in the step (3) is 9.0～11.0 according to each described method of claim 1-3.
13. method according to claim 12 is characterized in that described pH value is 9.5～10.5.
14., it is characterized in that adopting in the step (3) sodium bicarbonate, saleratus, yellow soda ash or salt of wormwood to regulate the pH value according to each described method of claim 1-3.
15. method according to claim 14 is characterized in that adopting in the step (3) sodium bicarbonate or saleratus to regulate the pH value.
16. method according to claim 1 is characterized in that comprising the steps: that (1) is water-soluble with Omeprazole Sodium, the solution adjusting pH value that adds solid acid salt is 6.5～7.0, stirs and separates out insolubles, filters, and obtains solid after the purified water washing; (2),,, collect elutriant with trichloromethane wash-out purifying through D101 macroporous adsorbent resin or AB-8 macroporous adsorbent resin with step (1) gained solid organic solvent dissolution; (3) step (2) gained elutriant being regulated pH value with sodium bicarbonate or saleratus is 9.5～10.5, separates out solid, centrifugal back washing with alcohol, and 30～40 ℃ of vacuum-drying 6～10 hours must the Omeprazole Sodium highly finished product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101834096A CN101412710B (en) | 2008-12-16 | 2008-12-16 | Omeprazole sodium compound and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101834096A CN101412710B (en) | 2008-12-16 | 2008-12-16 | Omeprazole sodium compound and preparation thereof |
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| CN101412710A CN101412710A (en) | 2009-04-22 |
| CN101412710B true CN101412710B (en) | 2010-04-21 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103570687B (en) * | 2013-11-15 | 2015-01-07 | 悦康药业集团有限公司 | Crystalline compound of omeprazole sodium |
| CN103788069B (en) * | 2014-02-26 | 2015-11-04 | 珠海润都制药股份有限公司 | The preparation method of esomeprazole magnesium trihydrate |
| CN104788426B (en) * | 2015-04-02 | 2015-12-30 | 天津大学 | A kind of Omeprazole Sodium semihydrate and preparation method thereof |
| CN112898272A (en) * | 2021-01-29 | 2021-06-04 | 海南葫芦娃药业集团股份有限公司 | Purification method for reducing omeprazole sodium impurity D |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1136564A (en) * | 1995-05-25 | 1996-11-27 | 常州市第四制药厂 | Aomeilazole salt hydrate for gastric acid inhibitor and its preparing method |
| CN1160050A (en) * | 1996-03-20 | 1997-09-24 | 常州市第四制药厂 | Process for refining omeprazole |
| CN1261362A (en) * | 1997-06-27 | 2000-07-26 | 阿斯特拉公司 | Omeprazole sodium salt |
-
2008
- 2008-12-16 CN CN2008101834096A patent/CN101412710B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1136564A (en) * | 1995-05-25 | 1996-11-27 | 常州市第四制药厂 | Aomeilazole salt hydrate for gastric acid inhibitor and its preparing method |
| CN1160050A (en) * | 1996-03-20 | 1997-09-24 | 常州市第四制药厂 | Process for refining omeprazole |
| CN1261362A (en) * | 1997-06-27 | 2000-07-26 | 阿斯特拉公司 | Omeprazole sodium salt |
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